Robert Bigger Oakley (born March 12, 1931) is a retired American diplomat. During his career as a Foreign Service Officer, Oakley served as United States Ambassador to Zaire, Somalia, and Pakistan, and later as a special envoy during the American involvement in Somalia in the early 1990s.
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Oakley joined the Foreign Service in 1957 and was assigned to Khartoum, Sudan, in 1958. He first served in the Office of United Nations Political Affairs, Department of State, and later served in American Embassies in Abidjan, Ivory Coast, Saigon, Vietnam, Paris, France, and Beirut, Lebanon. He also served at the U.S. Mission to the United Nations, and as Senior Director for Middle East and South Asia on the staff of the National Security Council.
In February 1977, he became Deputy to the Assistant Secretary of State for East Asia and Pacific Affairs. He later became U.S. Ambassador to Zaire in November 1979, and U.S. Ambassador to Somalia in August 1982. In September 1984, he was appointed Director of the State Department Office of Combating Terrorism. He again joined the National Security Council Staff on January 1, 1987, as Assistant to the President for Middle East and South Asia. He was named as U.S. Ambassador to Pakistan in August 1988, succeeding the late Arnold Lewis Raphel, who was killed in an airplane crash along with Pakistan's President, Muhammad Zia-ul-Haq.
Oakley retired from the Foreign Service in September 1991, after 34 years. After retirement, he became associated with the United States Institute of Peace. In December 1992, he was named by President George H. W. Bush as Special Envoy for Somalia, serving there with Operation Restore Hope until March 1993. In October 1993, he was again named as Special Envoy for Somalia by President Bill Clinton, and served in this capacity until March 1994. In January 1995, he joined the Institute for National Strategic Studies at the National Defense University. In 2000, prior to the September 11 attacks, Paul Bremer characterized the Clinton administration as "correctly focused on bin Laden", while Robert Oakley criticized their "obsession with Osama".
During his service with the State Department, Oakley received numerous State Department awards, including: the State Department Meritorious Honor Award, four Presidential Meritorious Service Awards, and the State Department Distinguished Honor Award. For his service as Special Envoy to Somalia, he received a second State Department Distinguished Honor Award and the Department of Defense Medal for Distinguished Public Service. On June 18, 1993, he received the Diplomatic Award for Excellence of the American Academy of Diplomacy. In October 2008, Oakley was awarded a Lifetime Achievement Award from Princeton in Africa.
Oakley married another Foreign Service Officer, Phyllis Elliott, in Cairo, Egypt, in June 1958. Under then-prevailing rules, Phyllis Oakley was obliged to resign. The Oakleys have two children, Mary Kress, and Thomas Oakley (one married, one divorced) and five grandchildren, Robert Kress, Andrew Kress, Peter Kress, Graham Oakley, and Josephine Oakley. Phyllis E. Oakley returned to the Foreign Service in 1974.
| Preceded by Walter L. Cutler |
U.S. Ambassador to Zaire 1979–1982 |
Succeeded by Peter Dalton Constable |
| Preceded by Donald K. Petterson |
U.S. Ambassador to Somalia 1982–1984 |
Succeeded by Peter Bridges |
| Preceded by Arnold Lewis Raphel |
U.S. Ambassador to Pakistan 1988–1991 |
Succeeded by Nicholas Platt |